Catalytic C-F Activation

We have recently discovered the first Pt-catalyzed cross-coupling reaction of C-F bonds. This methodology allows the construction of partially fluorinated aromatics, which are present in a wide range of pharmaceuticals, as well as optical and biomimetic materials. Methods for their construction remain a significant challenge and our methodology has the potential to provide access to a wide range of aryl fluoride synthetic building blocks. Preliminary investigations of reaction scope [Wang, T.; Alfonso, B. J.; Love, J. A. “Synthesis of Partially Fluorinated Aromatics via Pt-Catalyzed Cross Coupling of Aryl Fluorides, Org. Lett.2007, 9, 5629-5631] and mechanism [Wang, T.; Love, J. A. “Insight into the Mechanism of Pt-Catalyzed Cross-Coupling of Polyfluoroaryl Imines,” Organometallics2008, 27, 3290-3296] have been communicated. Current efforts include exploring the mechanism of reductive elimination from Pt(IV) [Wang, T.; Love, J. A. “Mechanism of Csp2-Csp3 Reductive Elimination from Pt(IV),” manuscript in preparation], as well as the development of a new strategy for aryl ether synthesis [Buckley, H. L.; Wang, T.; Love, J. A. “Aryl-Alkyl Ether Formation via Catalytic C-F Activation,” project underway]. We have also developed an efficient (non-catalytic) protocol for the synthesis of aryl ethers from the coupling of aryl fluorides with aryloxysilanes [Wang, T.; Love, J. A. “An Efficient Strategy for the Synthesis of Aryl Ethers,” Synthesis2007, 2237-2239 (Special issue)].

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